Hydrochloric Acid → (5,6-Dichloro-1H-indol-3-yl)acetic acid

HRID 588891Notes

Reaction equation

HRID 588891 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([O:15]CC)=[O:14].[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90460711HCID 90460711, compound

Product 1

HCID 13419487(5,6-Dichloro-1H-indol-3-yl)acetic acidYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-(5,6-dichloro-1H-indol-3-yl)acetate (120 mg, 0.44 mmol), LiOH (90 mg, 2.20 mmol) in THF (3 mL) and H2O (1 mL) was stirred at RT for 16 h. The solution was poured into water, adjusted pH to 3-4 with 1N HCl and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the desired product (90 mg, 84.5% yield) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-502ec2f94f184ffabb4eb5afae96a2e2
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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